The Secret Life of Dean Winchester
by Jayden Shay
Summary: <html><head></head>Dean's a whore. Not much else to it... Feel free to request what you want to see. Whore!Dean/OC, with possible wincest in later chapters.</html>
1. Streetwalker

"I'm heading out," Dean tells Sam, just as his brother's about to get in the shower, "maybe hit a bar or two, you know," His palms are sweaty, and his collar is too tight, but he resists the urge to give it a tug.

"You coming home tonight?" Sam asks, amused. He knows how this goes. Or… at least he thinks he does. Sam only knows what Dean tells him, something Dean tries not to feel too guilty about. Ignorance is bliss and all that, right?

He shoots his brother a winning smile over his shoulder as he heads out the door – the look that says everything for him – and finds it easy to look the part. After all, if everything goes according to plan, Dean _is_ getting laid tonight. Dimly, he registers Sam grinning as he shakes his head at Dean's departure.

It doesn't take Dean long to find a good street corner, so happy that they're finally in the city again instead of some crappy little apple-pie town where this kind of thing would never fly. Truth is: he's obsessed.

The first time he ever saw a hooker, Dean was with his dad, working a case. It was just one quick glimpse, but the memory never left him, and neither did the ideas that it stirred up. Why would someone ever choose to do that? What was it _like_? And some things are just better learned from experience, as Dean found out. His dad was away on a hunt, and Sam was staying with Bobby, and so Dean decided that he would try it out one night. Just like that, with no planning, and no idea what he was even getting into.

To say that they'd been holed up in a bad neighborhood was a bit of an understatement, and so, despite the fact that Dean had no idea what he was doing, nervously pacing the sidewalk, he'd gotten his first customer fairly quickly. At that point, unprepared had been the understatement of the century, and that was when Dean realized that he was in way over his head, but he went through with it anyway. It'd been the best night of his life, and at sixteen, he was hooked. Hooked on being a hooker… how ironic.

Now though, Dean knows what he's doing. In fact, he goes out whenever he can, whether he and Sam need the money or not. It's an addiction. He needs to feel used and abused, taken advantage of, rode hard and put up wet, it doesn't matter, but it gets him off and Dean loves every minute of it. He loves to lose control, to beg, to please – hell, he'll do anything, dirty little cocksucker that he is.

And Sam actually buys his crap about the chicks he supposedly meets in bars. Dean lives a complete double life, and his little brother, who he spends his whole life with practically, has no idea. If Dean isn't mistaken, Sam still thinks he's straight.

Soon, a potential trick is approaching Dean, and Dean puts on his best pout. His lips were just made to suck cock, and he knows it. The trick obviously does too, seeming to make up his mind about Dean in a blink. "Care for some company?" Dean calls out to him, doing his dammed best to look alluring. It works. Dean's not the best at what he does for nothing.

"How much?" The trick asks him, looking Dean up and down as if he's a piece of meat, which isn't the worst analogy for it. Dean will be anything the man wants him to be.

"Negotiable." He responds casually, leaning back against the wall behind him. It won't do to look _too,_ too eager, even if he totally is. The man is definitely good looking, which, although isn't always the case, is certainly a plus. Dean puts his age at around thirty-five, and he's dressed quite nicely; his clothes are definitely not of the cheap variety. He's got a bit of a shadow around his jaw, a full head of matching dark hair, and eyes that tell Dean that this man is used to being in control.

"I'll give you four hundred for the night," The man tells him, his voice low, and a bit gravelly which sends a shiver right up Dean's spine, but he keeps up the casual front.

"Make it five, half up front"

"And what will that get me?"

Dean grins in response. "Anything you want."

"Deal." The man agrees, and Dean's smile becomes seductive. He loves this job. The man pulls out a roll of bills to pay him, and Dean already can't wait to get started. He's come to know his customers in all of the years that he's been a whore, and this man looks like the type to enjoy a good kink or two. Currently, Dean's betting on handcuffs, and the solid metal kind, not the soft, fuzzy ones.

The trick takes him back to some ritzy hotel – business trip then – and they go up to the room together, Dean every bit as professional as the atmosphere demands. Well, up until they get to room 315, that is.

"You'll call me Sir, or Master," The trick informs him the second the door is shut, obviously not one to waste any time. Dean likes that. "And you'll respond to whatever I decide to call you. Got that slut?"

"Yes Master," Dean responds, and he's absolutely in heaven when he says it, even more so when his master for the night tells him to stay right where he is until he's told otherwise, the promise of more commands to come almost explicit.

"Is there a safe word I should be aware of?" The man asks then, crossing the room towards the bed and leaving Dean still standing by the door. He loosens his tie as he speaks, then takes it off entirely before placing it on the dresser, looped in half once. He's meticulous about things; just that one, simple action, and Dean can tell.

"Sammy," Dean says, knowing that there's probably something wrong with using his little brother's name as his safe word while he's whoring himself out, but he doesn't care. In fact, it just makes it that much more exciting, because Sam has absolutely no idea what he's doing right now. He'd hate it if he did, because Sam would never be able to understand that Dean practically lives for these nights. In fact, he can't get enough.

The man has no comment about that, simply repeats it once and it's so wrong hearing his brother's name come out of this man's lips that it's absolutely perfect. Dean can't wait to do what he's told, can't wait to be fucked into the bed, or the floor, or the dresser, or the wall…

Master takes a seat on the end of the bad, facing Dean, and Dean's almost trembling with the anticipation. "Strip." It's a simple command, and Dean gets to it right away. He tugs his shirt off – not too quickly, but not too slow either – and then begins to slide his pants down past his hips, slowly and sensually, inch by inch. His fingers glide across his bared abdomen, teasingly dipping below his ever-sinking waistband ever so often, and he loves the feel of the man's gaze on him, can practically feel the possessiveness there. It doesn't matter how many other guys Dean's fucked in the past – he's all Master's tonight.

By the time Dean's shed all of his clothes, there is a definite bulge in Master's pants, something that Dean wants to take care of very much. His eyes are drawn to it, slut that he is, and his mouth is watering with the knowledge that he will be soon.

"I want you on your hands and knees," Master commands him, and Dean sinks to the floor without a second thought, knowing that he's going to beg. And sure enough, "You're going to beg for my cock, whore, and if you do well, I just might let you have it," Dean can beg; in fact, it's another one of the things that he absolutely loves to do, and his own cock twitches just thinking about it.

"Please Master," Dean cajoles him, crawling towards the man on the bed with his ass in the air like the complete whore he is. "I need to taste you, want to take you deep in my throat," He's between the man's legs, looking up at him imploringly, his hot breath ghosting across the bulge in the man's pants, and Dean reaches up to unfasten them. "Oh, Master, please let me pleasure you,"

His fingers caress the button before he's drawing it open, nearly panting with his own need, but he takes it slow, fingering Master's errection through the material before undoing the zipper. He's being a tease and Dean' knows it, but the man seems to enjoy his reverent approach, because Dean is in no uncertain way, worshiping and savoring his cock with the anticipation.

Finally, Dean has worked Master's pants down to reveal his cock. It's long and hard, already tipped with pre-cum, which Dean tastes with a quick flick of his tongue. Delicious.

**AN: Evil place to break, I know. This was originally going to be a one-shot, but then it got a lot longer than I thought it would be, and I actually do have a life to keep up with, so... I should have the next chapter up sometime soon (like, tomorrow), and it's going to be EXPLICIT.**

**In the meantime, reviews are greatly appreciated, and feel free to suggest my next pairing!**


	2. Sweeter than a Lollipop

**Okay, well I just couldn't resist. Plus, I suck at Calculus, and it's giving me a headache... *smirks, while simultaneously recognizing the need to get my mind out of the gutter* I hope this is still decent despite my current brain cramp.**

"_Please Master," Dean cajoles him, crawling towards the man on the bed with his ass in the air like the complete whore he is. "I need to taste you, want to take you deep in my throat," He's between the man's legs, looking up at him imploringly, his hot breath ghosting across the bulge in the man's pants, and Dean reaches up to unfasten them. "Oh, Master, please let me pleasure you,"_

_His fingers caress the button before he's drawing it open, nearly panting with his own need, but he takes it slow, fingering Master's errection through the material before undoing the zipper. He's being a tease and Dean knows it, but the man seems to enjoy his reverent approach, because Dean is in no uncertain way, worshiping and savoring his cock with the anticipation._

_Finally, Dean has worked Master's pants down to reveal his cock. It's long and hard, already tipped with pre-cum, which Dean tastes with a quick flick of his tongue. Delicious._

Without a second thought, Dean parts his lips again, engulfing the head of his master's cock. He sucks gently, swirling his tongue around the hard length in his mouth before sucking again, more forcefully. Slowly, he draws the man deeper and deeper, licking and sucking. "Oh," Master breathes, and it sounds so much more obscene than it really should. Dean's own dick twitches with undeniable interest, but he just keeps on going. There is nothing Dean loves more than to pleasure someone else, and this is making him horny as hell.

"Deeper, Uhh," His tongue finds the sensitive underside as he descends and Dean toys with his master for a moment, pulling back before impaling himself further, and then again. His tongue is everywhere – swirling and flicking and teasing. He's practiced this after all; Dean knows how to make it good, and how to make it last.

The man somehow maintains his composure during this, smiling down at Dean in a patronizing way, even as he strokes Dean's hair – like one would an obedient dog. Its unnerving Dean though; he's never served anyone who wasn't desperate for his touch, who he couldn't reduce to a mushy pile of goo with his tongue alone. It's hot as all hell though. Dean would know.

Desperate for a reaction, desperate to please his master, Dean's pulling out all of the stops. With his hands, he massages the man's balls, while meanwhile he's giving it all he's got with his mouth on his dick. Cheeks hollowed out, Dean bobs his head along the sweet intrusion to his mouth, moaning and humming with pleasure. The tone is appreciative when Sir replies with, "You dirty, dirty bitch," His master's hips jerk up, but Dean's much too skilled to gag. He takes it like a pro, swallowing his master's entire length, as if he's never heard of the term 'gag-reflex'.

Finally, his master can't seem to take any more. "Such a damn slut, aren't you? Filthy cock-sucking whore," He gasps out, fisting his hands in Dean's hair. He forces Dean to deep-throat him again, now taking over the work. Dean's mouth is just a welcoming orifice to be fucked, hot and wet and ready. "Gonna fuck your face so hard," Master assures him, and does exactly that, thrusting into Dean's mouth over and over again, yanking him forwards by his hair every time.

It's the closest Dean has ever come to heaven, until Master is cumming down his throat, forcing Dean to swallow as he continues to ride out the aftershocks. The taste is amazing and indescribable – yeah, Dean knows it's just cum, for god's sakes, but it's so fucking hot and it's been much too long since he's done this – water to a man dying of thirst.

"Mmm, very good, slut." Master acknowledges, and then pushes Dean back before standing up. Dean is forced to bend awkwardly backwards, still in a kneeing position, but now resting back on his forearms, as his Master undresses himself. There's no stopping the quiet, fucked-out whimper that escapes Dean's lips as he sees the body being revealed to him, and betrays his longing to be used by it. There's a part of him that wanted to undress the man himself, but Dean goes along with this plan now, because, after all – he's not the one in charge. A slight shiver of pleasure runs through him again at that thought, his own all-but-forgotten cock stirring further. That isn't lost on his Master, who eyes him with some satisfaction as he takes a black duffle from behind the bed, not wasting any time.

In that instant, Dean knows. Master deftly unzips the bag, and even before Dean can see what's inside, he knows he's lucked upon one kinky son of a bitch.

**What particular kinks do you want to see? I'm as much of a whore as Dean, and I will gladly write anything. I'm a kinky bitch myself ;)**


End file.
